Pyridine → 2-(1-Chloro-2,2,2-trifluoroethyl)phenol

HRID 859650Notes

Reaction equation

HRID 859650 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:17])([F:16])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:6]([F:17])([F:16])[F:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 28292952-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

Product 1

HCID 587627412-(1-Chloro-2,2,2-trifluoroethyl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (2.28 ml) was added to a solution of 2-(2,2,2-trifluoro-1-hydroxyethyl)phenol (3.0 g) and pyridine (1.23 ml) in toluene (50 ml). The reaction was stirred at room temperature for 1 hr, after which time the toluene was removed in vacuuo and the residue partitioned between ethyl acetate (100 ml) and 1N HCl (100 ml). The organics were separated and dried over magnesium sulfate, filtered and solvent removed in vacuuo to afford the title compound as a clear oil (3.0 g). 1H NMR (CDCl3): δ 5.93 (m, 1H), 6.90 (d, J=4.52 Hz, 1H), 7.10 (m, 1H), 7.35 (m, 1H), 7.69 (m, 1H).

Workup

  1. customafter which time the toluene was removed in vacuuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and 1N HCl (100 ml)
  3. customThe organics were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed in vacuuo

Sources & evidence

ORD record
ord-3c01318fbecd41ad92004e5d5e63bd05
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

Loading…